Triethylamine → HCID 12451285, compound

HRID 1680906Notes

Reaction equation

HRID 1680906 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH3:5][NH:6][N:7]([CH3:17])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9].C(N(CC)CC)C>C(Cl)(Cl)Cl.ClCCl>[CH3:5][N:6]1[C:1](=[S:2])[N:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8](=[O:9])[N:7]1[CH3:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 12373507HCID 12373507, compound

Product 1

HCID 12451285HCID 12451285, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.26 g (0.037 mol) thiophosgene in about 10 ml chloroform was added dropwise to a solution of 6.7 g (0.037 mol) 1,2-dimethyl-4-phenylsemicarbazide and 7.47 g (0.074 mol) triethylamine in 200 ml chloroform. A slightly exothermic reaction ensued. One hour after the addition was completed, the reaction mixture was heated under reflux for about 16 hours, cooled and evaporated under reduced pressure to give an oil residue. The residue was dissolved in dichloromethane, washed with water, dried over magnesium sulfate, filtered and evaporated under reduced pressure to give a red viscous oil. The oil was chromatographed on 200 g of silica gel using dichloromethane as eluant. The major product (4 g) from the chromatography was a semisolid, which on trituration with ether gave the desired product as a light tan solid, m.p. 118°-122° C. Infrared spectrum of the product showed strong carbonyl absorption at 5.8 micron. The product is tabulated in Table I as Compound No. 1.

Workup

  1. customA slightly exothermic reaction
  2. additionOne hour after the addition
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for about 16 hours
  5. temperaturecooled
  6. customevaporated under reduced pressure
  7. customto give an oil residue
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure
  12. customto give a red viscous oil
  13. customThe oil was chromatographed on 200 g of silica gel

Sources & evidence

ORD record
ord-daacc1f379164c6c92db2b5c1e6c34c6
Source dataset
uspto-grants-1981_06
Patent number
US04276420

Reaction notes

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